Cannabidiol compositions having modified cannabinoid profiles
a technology of cannabinoid profiles and compositions, applied in the field of cannabinoid profiles modified cannabinoid profiles, can solve the problems of limited purity of availability of intermediate compounds, uncontrolled conversion of intermediate compounds to cyclized products,
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example 1
1) Preparation of Cannabidiol, (1′R,2′R)-5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diol
[0337]Cannabidiol was prepared according to the present disclosure.
Scheme 1-1—A Synthetic Route for the Preparation of 4,6-dibromo-Olivetol
[0338]
[0339]Olivetol (16.2 kg dry basis, 0.0897 kmol) was dissolved in dichloromethane (46 L / kg). The solution was cooled to −15° C., where it turned into a thin white suspension. Bromine (29.8 kg, 2.080 eq. with respect to Olivetol) was then added at −15° C. The reaction mixture transformed into a red solution at the end of the addition; no gas evolution was observed. The mixture dwelled for 5 min.
[0340]The process was monitored by IPC (In Process Control). Once the solution was compliant (NMT 0.5%, 4-monobromoolivetol) it was warmed to 0° C. and then poured over a solution of dipotassium hydrogenphosphate (47.2 kg) and sodium sulfite (1.1 kg) in demineralized water (290.9 kg), while maintaining the quench temperature be...
example 2
2) Preparation of Cannabidiol, (1′R,2′R)-5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diol
[0356]
Scheme 2-1—Synthesis of 4,6-dibromo-Olivetol
[0357]
[0358]Bromine (1.291 kg, 2.080 eq. with respect to Olivetol) was added to a suspension of Olivetol (0.7 kg, 3.88 mol) in dichloromethane (42 kg, 31.7 L) at −15° C. The reaction mixture was stirred for 5 min and then monitored by IPC to ensure complete conversion (NMT 0.5% 4-monobromoolivetol). An aqueous solution of dipotassium hydrogenphosphate (2.03 kg, 1.5 eq.), sodium hydroxide (0.233 kg, 1.5 eq.), and sodium sulfite (0.049 kg, 0.1 eq.) was then added to the mixture at 20° C. The lower organic phase was separated at 27° C. and dichloromethane was partially distilled off at atmospheric pressure to a volume of ˜6 mL / gOlivetol. Following this, n-Heptane was added (14.35 kg). The solution was further concentrated at 50° C. (900 to 200 mbar) to distill remaining dichloromethane azeotropically and reach a...
example 3
3) Preparation of Cannabidiol, (1′R,2′R)-5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diol
[0363]
Scheme 3-1—Synthesis of 4,6-dibromo-Olivetol
[0364]
[0365]Bromine (1.291 kg, 2.080 eq. with respect to Olivetol) was added to a suspension of Olivetol (0.7 kg, 3.88 mol) in dichloromethane (42 kg, 31.7 L) at −15° C. The reaction mixture was stirred for 5 min and then monitored by IPC to ensure complete conversion (NMT 0.5% 4-monobromoolivetol). An aqueous solution of dipotassium hydrogenphosphate (2.03 kg, 1.5 eq.), sodium hydroxide (0.233 kg, 1.5 eq.), and sodium sulfite (0.049 kg, 0.1 eq.) was added to the reaction mixture at 20° C. The lower organic phase was separated at 27° C. and dichloromethane was partially distilled off at atmospheric pressure to a volume of −6 mL / gOlivetol. Following this, n-heptane was added (14.35 kg). The solution was further concentrated at 50° C. (900 to 200 mbar) to distill the remaining dichloromethane azeotropically and...
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